Radical-nucleophilic aromatic substitution or SRN1 in organic chemistry is a type of substitution reaction in which a certain substituent on an aromatic compound is replaced by a nucleophile through an intermediary free radical species:
The substituent X is a halide and nucleophiles can be sodium amide, an alkoxide or a carbon nucleophile such as an enolate.[1] In contrast to regular nucleophilic aromatic substitution, deactivating groups on the arene are not required.[2]
This reaction type was discovered in 1970 by Bunnett and Kim[3] and the abbreviation SRN1 stands for substitution radical-nucleophilic unimolecular as it shares properties with an aliphatic SN1 reaction. An example of this reaction type is the Sandmeyer reaction.